IL307965A - Compounds and uses thereof - Google Patents
Compounds and uses thereofInfo
- Publication number
- IL307965A IL307965A IL307965A IL30796523A IL307965A IL 307965 A IL307965 A IL 307965A IL 307965 A IL307965 A IL 307965A IL 30796523 A IL30796523 A IL 30796523A IL 307965 A IL307965 A IL 307965A
- Authority
- IL
- Israel
- Prior art keywords
- optionally substituted
- compound
- cancer
- formula
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 70
- 125000000217 alkyl group Chemical group 0.000 claims 37
- 150000003839 salts Chemical class 0.000 claims 32
- 206010028980 Neoplasm Diseases 0.000 claims 24
- 201000011510 cancer Diseases 0.000 claims 24
- 239000008194 pharmaceutical composition Substances 0.000 claims 24
- 230000015556 catabolic process Effects 0.000 claims 23
- 238000006731 degradation reaction Methods 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 20
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 238000000034 method Methods 0.000 claims 14
- 125000004452 carbocyclyl group Chemical group 0.000 claims 13
- 229940127089 cytotoxic agent Drugs 0.000 claims 13
- 101000702545 Homo sapiens Transcription activator BRG1 Proteins 0.000 claims 11
- 102100031027 Transcription activator BRG1 Human genes 0.000 claims 11
- 206010006187 Breast cancer Diseases 0.000 claims 10
- 208000026310 Breast neoplasm Diseases 0.000 claims 10
- 210000004027 cell Anatomy 0.000 claims 10
- 125000004404 heteroalkyl group Chemical group 0.000 claims 10
- 206010005949 Bone cancer Diseases 0.000 claims 8
- 208000018084 Bone neoplasm Diseases 0.000 claims 8
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 201000001441 melanoma Diseases 0.000 claims 8
- 206010060862 Prostate cancer Diseases 0.000 claims 7
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 7
- 239000002246 antineoplastic agent Substances 0.000 claims 7
- 201000005787 hematologic cancer Diseases 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 230000000973 chemotherapeutic effect Effects 0.000 claims 6
- 239000002254 cytotoxic agent Substances 0.000 claims 6
- 231100000599 cytotoxic agent Toxicity 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 238000011319 anticancer therapy Methods 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 208000036142 Viral infection Diseases 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 230000004777 loss-of-function mutation Effects 0.000 claims 3
- 230000001394 metastastic effect Effects 0.000 claims 3
- 206010061289 metastatic neoplasm Diseases 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- -1 substituted Chemical class 0.000 claims 3
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 3
- 230000009385 viral infection Effects 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical group CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 claims 2
- 101710175516 14 kDa zinc-binding protein Proteins 0.000 claims 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 239000012275 CTLA-4 inhibitor Substances 0.000 claims 2
- 229940045513 CTLA4 antagonist Drugs 0.000 claims 2
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 2
- 239000012270 PD-1 inhibitor Substances 0.000 claims 2
- 239000012668 PD-1-inhibitor Substances 0.000 claims 2
- 239000012271 PD-L1 inhibitor Substances 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- 229940123924 Protein kinase C inhibitor Drugs 0.000 claims 2
- 229910020008 S(O) Inorganic materials 0.000 claims 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 claims 2
- YCPOZVAOBBQLRI-WDSKDSINSA-N Treosulfan Chemical compound CS(=O)(=O)OC[C@H](O)[C@@H](O)COS(C)(=O)=O YCPOZVAOBBQLRI-WDSKDSINSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 2
- 229960004316 cisplatin Drugs 0.000 claims 2
- 229960003901 dacarbazine Drugs 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- YAKWPXVTIGTRJH-UHFFFAOYSA-N fotemustine Chemical compound CCOP(=O)(OCC)C(C)NC(=O)N(CCCl)N=O YAKWPXVTIGTRJH-UHFFFAOYSA-N 0.000 claims 2
- 229960004783 fotemustine Drugs 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 229940043355 kinase inhibitor Drugs 0.000 claims 2
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229940121655 pd-1 inhibitor Drugs 0.000 claims 2
- 229940121656 pd-l1 inhibitor Drugs 0.000 claims 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- 239000003881 protein kinase C inhibitor Substances 0.000 claims 2
- 201000006845 reticulosarcoma Diseases 0.000 claims 2
- 208000029922 reticulum cell sarcoma Diseases 0.000 claims 2
- 239000000126 substance Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 229960004964 temozolomide Drugs 0.000 claims 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 2
- 229960003181 treosulfan Drugs 0.000 claims 2
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 241000701242 Adenoviridae Species 0.000 claims 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 229940122361 Bisphosphonate Drugs 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 229940123323 DNA repair enzyme inhibitor Drugs 0.000 claims 1
- 206010014733 Endometrial cancer Diseases 0.000 claims 1
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 208000006168 Ewing Sarcoma Diseases 0.000 claims 1
- 241000710781 Flaviviridae Species 0.000 claims 1
- 201000003741 Gastrointestinal carcinoma Diseases 0.000 claims 1
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims 1
- 208000021309 Germ cell tumor Diseases 0.000 claims 1
- 208000032612 Glial tumor Diseases 0.000 claims 1
- 206010018338 Glioma Diseases 0.000 claims 1
- 241000700739 Hepadnaviridae Species 0.000 claims 1
- 206010073073 Hepatobiliary cancer Diseases 0.000 claims 1
- 241000700586 Herpesviridae Species 0.000 claims 1
- 102000042838 JAK family Human genes 0.000 claims 1
- 108091082332 JAK family Proteins 0.000 claims 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 1
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 1
- 206010052178 Lymphocytic lymphoma Diseases 0.000 claims 1
- 208000032271 Malignant tumor of penis Diseases 0.000 claims 1
- 208000021541 MiT family translocation renal cell carcinoma Diseases 0.000 claims 1
- 208000009795 Microphthalmos Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 208000034176 Neoplasms, Germ Cell and Embryonal Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 241001631646 Papillomaviridae Species 0.000 claims 1
- 241000711504 Paramyxoviridae Species 0.000 claims 1
- 241000701945 Parvoviridae Species 0.000 claims 1
- 208000002471 Penile Neoplasms Diseases 0.000 claims 1
- 206010034299 Penile cancer Diseases 0.000 claims 1
- 241001631648 Polyomaviridae Species 0.000 claims 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
- 208000009052 Precursor T-Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 1
- 229940079156 Proteasome inhibitor Drugs 0.000 claims 1
- 241000712907 Retroviridae Species 0.000 claims 1
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 claims 1
- 206010061934 Salivary gland cancer Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims 1
- 208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 claims 1
- 208000037432 Thymic tumor Diseases 0.000 claims 1
- 208000000728 Thymus Neoplasms Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 241000710924 Togaviridae Species 0.000 claims 1
- 108091023040 Transcription factor Proteins 0.000 claims 1
- 102000040945 Transcription factor Human genes 0.000 claims 1
- 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 201000005969 Uveal melanoma Diseases 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 201000011186 acute T cell leukemia Diseases 0.000 claims 1
- 108700010877 adenoviridae proteins Proteins 0.000 claims 1
- 208000020990 adrenal cortex carcinoma Diseases 0.000 claims 1
- 208000007128 adrenocortical carcinoma Diseases 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 230000000340 anti-metabolite Effects 0.000 claims 1
- 230000002927 anti-mitotic effect Effects 0.000 claims 1
- 230000000118 anti-neoplastic effect Effects 0.000 claims 1
- 229940100197 antimetabolite Drugs 0.000 claims 1
- 239000002256 antimetabolite Substances 0.000 claims 1
- 239000003972 antineoplastic antibiotic Substances 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 208000021780 appendiceal neoplasm Diseases 0.000 claims 1
- 229960001230 asparagine Drugs 0.000 claims 1
- 235000009582 asparagine Nutrition 0.000 claims 1
- 150000004663 bisphosphonates Chemical class 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 208000030381 cutaneous melanoma Diseases 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 239000012649 demethylating agent Substances 0.000 claims 1
- 208000014616 embryonal neoplasm Diseases 0.000 claims 1
- 201000007028 gastrointestinal neuroendocrine tumor Diseases 0.000 claims 1
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 229940121372 histone deacetylase inhibitor Drugs 0.000 claims 1
- 239000003276 histone deacetylase inhibitor Substances 0.000 claims 1
- 230000002519 immonomodulatory effect Effects 0.000 claims 1
- 229940099472 immunoglobulin a Drugs 0.000 claims 1
- 238000009169 immunotherapy Methods 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 201000002313 intestinal cancer Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000010478 microphthalmia Diseases 0.000 claims 1
- 201000003731 mucosal melanoma Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000000649 photocoagulation Effects 0.000 claims 1
- 239000003207 proteasome inhibitor Substances 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 201000008261 skin carcinoma Diseases 0.000 claims 1
- 201000003708 skin melanoma Diseases 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 238000000015 thermotherapy Methods 0.000 claims 1
- 201000009377 thymus cancer Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 208000022679 triple-negative breast carcinoma Diseases 0.000 claims 1
- 208000036907 triple-positive breast carcinoma Diseases 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 208000037965 uterine sarcoma Diseases 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
Claims (50)
1. A compound, or a pharmaceutically acceptable salt thereof, having the structure of Formula I or II : , Formula I Formula II wherein ring system A is a 5 to 9-membered heterocyclyl or heteroaryl; m is 0, 1, 2, or 3; k is 0, 1, or 2; each R is, independently, halo, optionally substituted C-C alkyl, optionally substituted C-C heteroalkyl, optionally substituted C-C cycloalkyl, or optionally substituted C-C heterocyclyl; each X is, independently, halo; L is a linker; and B is a degradation moiety.
2. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound has the structure of Formula I-A or II-A : , Formula I-A Formula II-Awherein the dashed bond represents a single or double bond; or, wherein the compound has the structure of Formula I-B : PATENT ATTORNEY DOCKET NO.: 51121-071WO . Formula I-B ; or,, wherein the compound has the structure of Formula I-C : , Formula I-C wherein each R is, independently, optionally substituted C-C alkyl; or, . wherein the compound has the structure of Formula I-D : , Formula I-D wherein each R is, independently, optionally substituted C-C alkyl; or, . wherein the compound has the structure of Formula I-E : PATENT ATTORNEY DOCKET NO.: 51121-071WO . Formula I-E ; or, wherein the compound has the structure of Formula I-F : . Formula I-F
3. The compound of claim 1 or claim 2, or a pharmaceutically acceptable salt thereof, wherein m is 0.
4. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein the compound has the structure of Formula I-G or II-G : , . Formula I-G Formula II-G ; or,, wherein the compound has the structure of Formula I-H or II-H : PATENT ATTORNEY DOCKET NO.: 51121-071WO , . Formula I-H Formula II-H
5. The compound of any one of claims 1 to 10, or a pharmaceutically acceptable salt thereof, wherein the degradation moiety, B, has the structure of Formula A-1 : , Formula A-1 wherein Y is , , , or ; RA5 is H, optionally substituted C-C alkyl, or optionally substituted C-Cheteroalkyl; RA6 is H or optionally substituted C-C alkyl; and RA7 is H or optionally substituted C-C alkyl; or RA6 and RA7, together with the carbon atom to which each is bound, combine to form optionally substituted C-Ccarbocyclyl or optionally substituted C-C heterocyclyl; or RA6 and RA7, together with the carbon atom to which each is bound, combine to form optionally substituted C-Ccarbocyclyl or optionally substituted C-C heterocyclyl; RA8 is H, optionally substituted C-C alkyl, or optionally substituted C-Cheteroalkyl; each of RA1, RA2, RA3, and RA4 is, independently, H, A, halogen, optionally substituted C-Calkyl, optionally substituted C-Cheteroalkyl, optionally substituted C-C carbocyclyl, optionally substituted C-C heterocyclyl, optionally substituted C-C aryl, optionally substituted C-C heteroaryl, optionally substituted C-C alkenyl, optionally substituted C-C heteroalkenyl, optionally substituted -O-C-C carbocyclyl, hydroxyl, thiol, or optionally substituted amino; or RA1 and RA2, RA2 and RA3, and/or RA3 and RA4, together with the carbon atoms to which each is attached, combine to form ; and is optionally substituted C-C aryl, optionally substituted C-C carbocyclyl, optionally substituted C-C heteroaryl, or C-C heterocyclyl, any of which is optionally substituted with A, where one of RA1, RA2, RA3, and RA4 is A, or is substituted with A; and A is a bond between the degradation moiety and the linker. PATENT ATTORNEY DOCKET NO.: 51121-071WO
6. The compound of claim 5, or a pharmaceutically acceptable salt thereof, wherein RA5 is H or methyl; wherein each of RA1, RA2, RA3, and RA4 is, independently, H or A; wherein RA1 is A and each of RA2, RA3, and RAis H; wherein RA2 is A and each of RA1, RA3, and RAis H; wherein RA3 is A and each of RA1, RA2, and RAis H; and, wherein RA4 is A and each of RA1, RA2, and RAis H. 7. The compound of claim 5 or 6, or a pharmaceutically acceptable salt thereof, wherein Y is or ; RA6 is H; and RA7 is H. 8. The compound of any one of claims 5 to 7, or a pharmaceutically acceptable salt thereof, wherein Y is or ; RA8 is H or optionally substituted C-C alkyl, preferably methyl. 9. The compound of any one of claims 5 to 8, or a pharmaceutically acceptable salt thereof, wherein the degradation moiety comprises the structure of Formula A2 :
7.; Formula A2 ; or, wherein the degradation moiety comprises the structure of Formula A4 : ; or Formula A4
8.PATENT ATTORNEY DOCKET NO.: 51121-071WO wherein the degradation moiety comprises the structure of Formula A5 : ; or, Formula A5 wherein the degradation moiety comprises the structure of Formula A6 : ; or, Formula A6 wherein the degradation moiety comprises the structure of Formula A8 : ; or, Formula A8 wherein the degradation moiety comprises the structure of Formula A10 : ; or, Formula A10 wherein the degradation moiety comprises the structure of .
9.PATENT ATTORNEY DOCKET NO.: 51121-071WO wherein the degradation moiety comprises the structure of
10. 10. The compound of claim 2 or 9, or a pharmaceutically acceptable salt thereof, wherein the degradation moiety is ; or, .
11. The compound of any one of claims 1 to 10, or a pharmaceutically acceptable salt thereof, wherein the degradation moiety has the structure of Formula C ’ : , Formula C ’ wherein L is -N(RB1)(RB2), , , or ; RB1 is H, A, optionally substituted C-C alkyl, or optionally substituted C-Cheteroalkyl;RB2 is H, optionally substituted C-C alkyl, optionally substituted C-C heterocyclyl, or optionally substituted C-Cheteroalkyl; RB3 is A, optionally substituted C-C alkyl, optionally substituted C-C heteroalkyl, optionally substituted C-C carbocyclyl, optionally substituted C-C aryl, optionally substituted C-C alkyl C-C carbocyclyl, or optionally substituted C-C alkyl C-C aryl; RB4 is H, optionally substituted C-C alkyl, optionally substituted C-C carbocyclyl, optionally substituted C-C aryl, optionally substituted C-C alkyl C-C carbocyclyl, or optionally substituted C-C alkyl C-C aryl; RB5 is H, optionally substituted C-C alkyl, or optionally substituted C-Cheteroalkyl; v2 is 0, 1, 2, 3, or 4; each RB6 is, independently, A, halogen, optionally substituted C-Calkyl, optionally substituted C-Cheteroalkyl, optionally substituted C-C carbocyclyl, optionally substituted C-C heterocyclyl, PATENT ATTORNEY DOCKET NO.: 51121-071WO optionally substituted C-C aryl, optionally substituted C-C heteroaryl, optionally substituted C-C alkenyl, optionally substituted C-C heteroalkenyl, hydroxy, thiol, or optionally substituted amino; each of RB7 and RB8 is, independently, H, halogen, optionally substituted C-C alkyl, or optionally substituted C-C aryl; RB9 is H or optionally substituted C-C alkyl; and A is a bond between the degradation moiety and the linker; wherein one and only one of RB1, RB3, and RB6 is A, or a pharmaceutically acceptable salt thereof.
12. The compound of any one of claims 1 to 11, or a pharmaceutically acceptable salt thereof, wherein the degradation moiety has the structure of Formula C : , Formula C wherein L is -N(RB1)(RB2), or ; RB1 is H, A, optionally substituted C-C alkyl, or optionally substituted C-Cheteroalkyl; RB2 is H, optionally substituted C-C alkyl, or optionally substituted C-Cheteroalkyl; RB3 is A, optionally substituted C-C alkyl, optionally substituted C-C heteroalkyl, optionally substituted C-C carbocyclyl, optionally substituted C-C aryl, optionally substituted C-C alkyl C-C carbocyclyl, or optionally substituted C-C alkyl C-C aryl; RB4 is H, optionally substituted C-C alkyl, optionally substituted C-C carbocyclyl, optionally substituted C-C aryl, optionally substituted C-C alkyl C-C carbocyclyl, or optionally substituted C-C alkyl C-C aryl; RB5 is H, optionally substituted C-C alkyl, or optionally substituted C-Cheteroalkyl; v2 is 0, 1, 2, 3, or 4; each RB6 is, independently, A, halogen, optionally substituted C-Calkyl, optionally substituted C-Cheteroalkyl, optionally substituted C-C carbocyclyl, optionally substituted C-C heterocyclyl, optionally substituted C-C aryl, optionally substituted C-C heteroaryl, optionally substituted C-C alkenyl, optionally substituted C-C heteroalkenyl, hydroxy, thiol, or optionally substituted amino; each of RB7 and RB8 is, independently, H, halogen, optionally substituted C-C alkyl, or optionally substituted C-C aryl; RB9 is H or optionally substituted C-C alkyl; and A is a bond between the degradation moiety and the linker; PATENT ATTORNEY DOCKET NO.: 51121-071WO wherein one and only one of RB1, RB3, and RB6 is A, or a pharmaceutically acceptable salt thereof.
13. The compound of claim 11 or 12, or a pharmaceutically acceptable salt thereof, wherein the degradation moiety has the structure of Formula C1 : ; or, Formula C1 wherein the degradation moiety is ; or, wherein the degradation moiety is ; or ; or, wherein the degradation moiety has the structure of Formula C2 : PATENT ATTORNEY DOCKET NO.: 51121-071WO ; or Formula C2 wherein the degradation moiety is
14. The compound of any one of claims 11-13, or a pharmaceutically acceptable salt thereof, wherein RB9 is optionally substituted C-C alkyl, preferably methyl, and wherein RB9 is bonded to (S)-stereogenic center. 15. The compound of any one of claims 1 to 14, or a pharmaceutically acceptable salt thereof, wherein the linker has the structure of Formula III : A-(B)f-(C)g-(B)h-(D)-(B)i-(C)j-(B)k–A, Formula IIIor a pharmaceutically acceptable salt thereof, wherein; A is a bond between the linker and ring system A; A is a bond between the degradation moiety and the linker; each of B, B, B, and B is, independently, optionally substituted C-C alkyl, optionally substituted C-C aryl, optionally substituted C-C aryl C1-4 alkyl, optionally substituted C-C heteroalkyl, optionally substituted C-C cycloalkyl, optionally substituted C-C heterocyclyl, optionally substituted C-C heteroaryl, O, S, S(O), or NRN; each RN is, independently, H, optionally substituted C1–4 alkyl, optionally substituted C2–4 alkenyl, optionally substituted C2–4 alkynyl, optionally substituted C2–6 heterocyclyl, optionally substituted C6–12 aryl, or optionally substituted C1–7 heteroalkyl; each of C and C is, independently, carbonyl, thiocarbonyl, sulphonyl, or phosphoryl; each of f, g, h, i, j, and k is, independently, 0 or 1; and D is optionally substituted C1–10 alkyl, optionally substituted C2–10 alkenyl, optionally substituted C2–10 alkynyl, optionally substituted C2–6 heterocyclyl, optionally substituted C6–12 aryl, optionally
15.PATENT ATTORNEY DOCKET NO.: 51121-071WO substituted C-C polyethylene glycol, or optionally substituted C1–10 heteroalkyl, or a chemical bond linking A-(B)f-(C)g-(B)h- to -(B)i-(C)j-(B)k–A.
16. The compound of any one of claims 1 to 14, or a pharmaceutically acceptable salt thereof, wherein the linker has the structure of Formula III : A-(B)f-(C)g-(B)h-(D)-(B)i-(C)j-(B)k–A, Formula IIIor a pharmaceutically acceptable salt thereof, wherein; A is a bond between the linker and ring system A; A is a bond between the degradation moiety and the linker; each of B, B, B, and B is, independently, optionally substituted C-C alkyl, optionally substituted C-C aryl, optionally substituted C-C aryl C1-4 alkyl, optionally substituted C-C heteroalkyl, optionally substituted C-C cycloalkyl, optionally substituted C-C heterocyclyl, O, S, S(O), or NRN; each RN is, independently, H, optionally substituted C1–4 alkyl, optionally substituted C2–4 alkenyl, optionally substituted C2–4 alkynyl, optionally substituted C2–6 heterocyclyl, optionally substituted C6–12 aryl, or optionally substituted C1–7 heteroalkyl; each of C and C is, independently, carbonyl, thiocarbonyl, sulphonyl, or phosphoryl; each of f, g, h, i, j, and k is, independently, 0 or 1; and D is optionally substituted C1–10 alkyl, optionally substituted C2–10 alkenyl, optionally substituted C2–10 alkynyl, optionally substituted C2–6 heterocyclyl, optionally substituted C6–12 aryl, optionally substituted C-C polyethylene glycol, or optionally substituted C1–10 heteroalkyl, or a chemical bond linking A-(B)f-(C)g-(B)h- to -(B)i-(C)j-(B)k–A.
17. The compound of claim 15 or 16, or a pharmaceutically acceptable salt thereof, wherein each of B, B, B, and B is, independently, optionally substituted C-C alkyl, optionally substituted C-C heteroalkyl, optionally substituted C-C heterocyclyl, or NRN, or, wherein each RN is, independently, H or optionally substituted C–C alkyl, preferably, methyl.
18. The compound of any one of claims 15 to 17, or a pharmaceutically acceptable salt thereof, wherein each of B and B is, independently, O, , , , , , , , , , , , , , PATENT ATTORNEY DOCKET NO.: 51121-071WO , , , , , , , , , , , or .
19. The compound of claim 15 to 18, or a pharmaceutically acceptable salt thereof, wherein each of C and C is or .
20. The compound of any one of claims 15 to 19, or a pharmaceutically acceptable salt thereof, wherein B is optionally substituted C-C alkyl, optionally substituted C-C heterocyclyl, or , optionally substituted C-C heteroaryl, , or, optionally substituted C-C cycloalkyl; B is , D is optionally substituted C-C alkyl; f is 1; g is 0 or 1; h is 0 or 1; i is 0 or 1; j is 0 or 1; k is 0, or 1. PATENT ATTORNEY DOCKET NO.: 51121-071WO
21. The compound of any one of claims 15 to 20, or a pharmaceutically acceptable salt thereof, wherein the linker has the structure of , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , PATENT ATTORNEY DOCKET NO.: 51121-071WO , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , PATENT ATTORNEY DOCKET NO.: 51121-071WO , , , , , , , , , , , , , , , , , , , , , , , , , , , , or
22. 22. The compound of any one of claims 15 to 21, or a pharmaceutically acceptable salt thereof, wherein the linker has the structure of , , , , , , PATENT ATTORNEY DOCKET NO.: 51121-071WO , , , , , , , , , , , , , , , , , , , , , , , , , , , PATENT ATTORNEY DOCKET NO.: 51121-071WO , , , , , , , , , , , , , , , , , , , or .
23. The compound of any one of claims 15 to 22, or a pharmaceutically acceptable salt thereof, wherein the shortest chain of atoms connecting two valencies of the linker is 2 to 10 atoms long.
24. The compound of any one of claims 15 to 22, or a pharmaceutically acceptable salt thereof, wherein the shortest chain of atoms connecting two valencies of the linker is 6 atoms long.
25. The compound of claim 23, or a pharmaceutically acceptable salt thereof, wherein the linker has the structure of , , , , , , ,
26.PATENT ATTORNEY DOCKET NO.: 51121-071WO , , , , , , , , ,or . 26. A compound selected from the group consisting of compounds 1-33 in Table 1 and pharmaceutically acceptable salts thereof.
27. A compound selected from the group consisting of compounds 1-115 in Table 1 and pharmaceutically acceptable salts thereof.
28. The compound of any one of claims 1 to 86, or a pharmaceutically acceptable salt thereof, wherein the compound has a ratio of BRG1 IC to BRM IC of at least 5; wherein the compound has a ratio of BRG1 IC to BRM IC of at least 7; wherein the compound has a ratio of BRG1 IC to BRM IC of at least 10; wherein the compound has a ratio of BRG1 IC to BRM IC of at least 15; wherein the compound has a ratio of BRG1 IC to BRM IC of at least 20; wherein the compound has a ratio of BRG1 IC to BRM IC of at least 25; wherein the compound has a ratio of BRG1 IC to BRM IC of at least 30.
29. A pharmaceutical composition comprising a compound of any one of claims 1 to 28 and a pharmaceutically acceptable excipient.
30. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of decreasing the activity of a BAF complex in a cell; wherein the BAF complex is in a cancer cell.
31. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of treating a BAF complex-related disorder in a subject in need thereof, wherein the BAF complex-related disorder is cancer or a viral infection.
32. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of inhibiting BRM, PATENT ATTORNEY DOCKET NO.: 51121-071WO wherein the cell is a cancer cell.
33. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of treating a disorder related to a BRG1 loss of function mutation in a subject in need thereof, wherein the disorder related to a BRG1 loss of function mutation is cancer.
34. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of inducing apoptosis in a cell, wherein the cell is a cancer cell.
35. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of treating cancer in a subject in need thereof.
36. The compound or pharmaceutical composition for use of any one of claims 30 -35, wherein the cancer is non-small cell lung cancer, colorectal cancer, bladder cancer, cancer of unknown primary, glioma, breast cancer, melanoma, non-melanoma skin cancer, endometrial cancer, esophagogastric cancer, pancreatic cancer, hepatobiliary cancer, soft tissue sarcoma, ovarian cancer, head and neck cancer, renal cell carcinoma, bone cancer, non-Hodgkin lymphoma, small-cell lung cancer, prostate cancer, embryonal tumor, germ cell tumor, cervical cancer, thyroid cancer, salivary gland cancer, gastrointestinal neuroendocrine tumor, uterine sarcoma, gastrointestinal stromal tumor, CNS cancer, thymic tumor, Adrenocortical carcinoma, appendiceal cancer, small bowel cancer, or penile cancer.
37. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of treating a cancer selected from the group consisting of melanoma, prostate cancer, breast cancer, bone cancer, renal cell carcinoma, and a hematologic cancer in a subject in need thereof.
38. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of reducing tumor growth of a cancer selected from the group consisting of melanoma, prostate cancer, breast cancer, bone cancer, renal cell carcinoma, and a hematologic cancer in a subject in need thereof.
39. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of suppressing metastatic progression of a cancer selected from the group consisting of melanoma, prostate cancer, breast cancer, bone cancer, renal cell carcinoma, and a hematologic cancer in a subject.
40. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of suppressing metastatic colonization of a cancer selected from the group consisting of melanoma, prostate cancer, breast cancer, bone cancer, renal cell carcinoma, and a hematologic cancer in a subject. PATENT ATTORNEY DOCKET NO.: 51121-071WO
41. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of reducing the level and/or activity of BRG1 and/or BRM in a cancer selected from the group consisting of melanoma, prostate cancer, breast cancer, bone cancer, renal cell carcinoma, and hematologic cancer cell, optionally, wherein the cell is in a subject.
42. The compound or pharmaceutical composition for use of any one of claims 37 to 41, wherein the cancer is metastatic. 42. The compound or pharmaceutical composition for use of any one of claims 37 to 42, wherein the method further comprises administering to the subject or contacting the cell with an anticancer therapy; wherein the anticancer therapy is a chemotherapeutic or cytotoxic agent, immunotherapy, surgery, radiotherapy, thermotherapy, or photocoagulation, wherein the anticancer therapy is a chemotherapeutic or cytotoxic agent; wherein the chemotherapeutic or cytotoxic agent is an antimetabolite, antimitotic, antitumor antibiotic, asparagine-specific enzyme, bisphosphonates, antineoplastic, alkylating agent, DNA-Repair enzyme inhibitor, histone deacetylase inhibitor, corticosteroid, demethylating agent, immunomodulatory, janus-associated kinase inhibitor, phosphinositide 3-kinase inhibitor, proteasome inhibitor, or tyrosine kinase inhibitor, wherein the one or more chemotherapeutic or cytotoxic agent is dacarbazine, temozolomide, cisplatin, treosulfan, fotemustine, IMCgp100, a CTLA-4 inhibitor, a PD-1 inhibitor, a PD-L1 inhibitor, a mitogen-activated protein kinase inhibitor, and/or a protein kinase C inhibitor.
43. The compound or pharmaceutical composition for use of claim 42 or 43, wherein the anticancer therapy and the compound of any one of claims 1 to 24 or a pharmaceutical composition of claim 25 are administered within 28 days of each other and each in an amount that together are effective to treat the subject; wherein the subject or cancer has and/or has been identified as having a BRG1 loss of function mutation, wherein the cancer has failed to respond to or progressed after administration of one or more chemotherapeutic or cytotoxic agents, or, wherein the cancer is resistant to, or predicted to be resistant to one or more chemotherapeutic agents.
44. The compound or pharmaceutical composition for use of claim 42 or 43, wherein the one or more chemotherapeutic or cytotoxic agents is dacarbazine, temozolomide, cisplatin, treosulfan, fotemustine, IMCgp100, a CTLA-4 inhibitor, a PD-1 inhibitor, a PD-L1 inhibitor, a mitogen-activated protein kinase inhibitor, and/or a protein kinase C inhibitor; wherein the cancer is melanoma, PATENT ATTORNEY DOCKET NO.: 51121-071WO wherein the melanoma is uveal melanoma, mucosal melanoma, or cutaneous melanoma.
45. The compound or pharmaceutical composition for use of any one of claims 42 to 44, wherein the cancer is a hematologic cancer, wherein the hematologic cancer is multiple myeloma, large cell lymphoma, acute T-cell leukemia, acute myeloid leukemia, myelodysplastic syndrome, immunoglobulin A lambda myeloma, diffuse mixed histiocytic and lymphocytic lymphoma, B-cell lymphoma, acute lymphoblastic leukemia, diffuse large cell lymphoma, or non-Hodgkin’s lymphoma.
46. The compound or pharmaceutical composition for use of any one of claims 37 to 44, wherein the cancer is prostate cancer.
47. The compound or pharmaceutical composition for use of any one of claims 37 to 44, wherein the cancer is breast cancer, wherein the breast cancer is an ER positive breast cancer, an ER negative breast cancer, triple positive breast cancer, or triple negative breast cancer. 47. The compound or pharmaceutical composition for use of any one of claims 37 to 44, wherein the cancer is bone cancer, wherein the bone cancer is Ewing’s sarcoma.
48. The compound or pharmaceutical composition for use of any one of claims 37 to 44, wherein the cancer is renal cell carcinoma, wherein the renal cell carcinoma is Microphthalmia Transcription Factor (MITF) family translocation renal cell carcinoma.
49. A compound of any one of claims 1 to 28 or a pharmaceutical composition of claim 29 for use in a method of treating a viral infection in a subject in need thereof.
50. The method of claim 49, wherein the viral infection is an infection with a virus of the Retroviridae family, Hepadnaviridae family, Flaviviridae family, Adenoviridae family, Herpesviridae family, Papillomaviridae family, Parvoviridae family, Polyomaviridae family, Paramyxoviridae family, or Togaviridae family.
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CN112771038A (en) * | 2018-04-26 | 2021-05-07 | 奥里吉恩发现科技有限公司 | Pyridazine derivatives as SMARCA2/4 degradants |
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